1-Bromo-3,5-dinitrobenzene → ar-Bromo-ar-nitrobenzenamine

HRID 64083

Reaktionsgleichung

Reaktionsgleichung von HRID 64083
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1)[NH2:8]

Komponenten

4

Edukt 1

HCID 445341-Bromo-3,5-dinitrobenzene

Produkt 1

HCID 44535ar-Bromo-ar-nitrobenzenamineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 1-bromo-3,5-dinitrobenzene (20 g, 80.97 mmol) in acetic acid (120 ml) at 90° C. was added iron powder (11.3 g, 202.4 mmol, 2.5 eq) slowly portionwise over a period of 30 min (caution: highly exothermic reaction). After completion of the addition, the mixture was quenched by the addition of crushed ice. The precipitate formed was filtered and was washed with cold water to obtain orange solid. The solid was dried under vacuum to give the product in 80% yield (14 g). 1H NMR (300 MHz, CDCl3): δ 10.55 (br s, 2H), 8.46 (s, 1H), 8.19 (s, 1H), 8.02 (s, 1H).

Aufarbeitung

  1. customhighly exothermic reaction)
  2. additionAfter completion of the addition
  3. customthe mixture was quenched by the addition of crushed ice
  4. customThe precipitate formed
  5. filtrationwas filtered
  6. washwas washed with cold water
  7. customto obtain orange solid
  8. customThe solid was dried under vacuum
  9. customto give the product in 80% yield (14 g)

Quellen und Nachweise

ORD-Eintrag
ord-753a8f480966446dafb69e87c8975f55
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447091B2

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